Social Security benefits depend on the employment and earnings history of the covered worker, but, especially for women, they depend on one’s marital history and the employment and earnings history of one’s spouse. This study examines the interrelationship between marriage, divorce, employment and earnings of men and women. Since getting married (or getting divorced) tends to affect women’s employment choices differently than men’s, we consider the sexes separately. We estimate: (1) the impact of earnings, work hours and wages while unmarried on the likelihood of (re)marriage, (2) the effect of these measures of career success while married on the likelihood of divorce; (3) the effect of being married on men’s and women’s propensity to participate in the labor force, and conditional on participation, the effect of being married on earnings, wages and annual hours of work; for all these labor market outcomes we also assess the impact of the length of the marriage. Together, these results show a pattern of gender specialization in marriage, with men moving toward and women moving away from more intensive and extensive employment and the financial gain it brings. Success in the labor market while single increases the likelihood of marriage for men and decreases it for women. More work and greater financial rewards from work tend to stabilize marriage for men and destabilize marriage for women. Our results also show substantial change in the relationship between marital and employment careers for those born after WWII, but only for women. The employment careers of younger women are much less responsive to marriage than were those of their mothers or older sisters.